In an effort to provide insights into the relationship between poly-N-acrylamide tacticity and conformation, we set out to generate a series of N-acrylamide oligomers of well-defined length and backbone stereochemistry by non-polymerizing synthetic strategies 6 and correlate unambiguously their conformational preferences and hydrogen bonding propensities with the backbone stereochemistry (tacticity). Herein we report the synthesis, and structural studies of a series of N-alkyl ...